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MedKoo Cat#: 558569 | Name: Coniine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Coniine is an alkaloid isolated from Conium maculatum L. It has properties as an analgesic, antineuralgic, & teratogen.

Chemical Structure

Coniine
CAS#458-88-8

Theoretical Analysis

MedKoo Cat#: 558569

Name: Coniine

CAS#: 458-88-8

Chemical Formula: C8H17N

Exact Mass: 127.1400

Molecular Weight: 127.23

Elemental Analysis: C, 75.52; H, 13.47; N, 11.01

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Coniine; Cicutin; Cicutine; Conicine;
IUPAC/Chemical Name
CCC[C@@H]1NCCCC1
InChi Key
NDNUANOUGZGEPO-QMMMGPOBSA-N
InChi Code
InChI=1S/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3/t8-/m0/s1
SMILES Code
CCC[C@@H]1NCCCC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 127.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Green BT, Lee ST, Welch KD, Pfister JA, Panter KE. Fetal muscle-type nicotinic acetylcholine receptor activation in TE-671 cells and inhibition of fetal movement in a day 40 pregnant goat model by optical isomers of the piperidine alkaloid coniine. J Pharmacol Exp Ther. 2013 Jan;344(1):295-307. doi: 10.1124/jpet.112.199588. Epub 2012 Oct 19. PubMed PMID: 23086230. 2: Lee ST, Green BT, Welch KD, Pfister JA, Panter KE. Stereoselective potencies and relative toxicities of coniine enantiomers. Chem Res Toxicol. 2008 Oct;21(10):2061-4. doi: 10.1021/tx800229w. Epub 2008 Sep 3. PubMed PMID: 18763813. 3: Forsyth CS, Frank AA. Evaluation of developmental toxicity of coniine to rats and rabbits. Teratology. 1993 Jul;48(1):59-64. PubMed PMID: 8351649. 4: Forsyth CS, Frank AA, Watrous BJ, Bohn AA. Effect of coniine on the developing chick embryo. Teratology. 1994 Apr;49(4):306-10. PubMed PMID: 8073369. 5: Arihan O, Boz M, Iskit AB, Ilhan M. Antinociceptive activity of coniine in mice. J Ethnopharmacol. 2009 Sep 7;125(2):274-8. doi: 10.1016/j.jep.2009.06.032. Epub 2009 Jul 4. PubMed PMID: 19580858. 6: Forsyth CS, Speth RC, Wecker L, Galey FD, Frank AA. Comparison of nicotinic receptor binding and biotransformation of coniine in the rat and chick. Toxicol Lett. 1996 Dec 31;89(3):175-83. PubMed PMID: 9001585. 7: Keeler RF, Balls LD, Shupe JL, Crowe MW. Teratogenicity and toxicity of coniine in cows, ewes, and mares. Cornell Vet. 1980 Jan;70(1):19-26. PubMed PMID: 7379551. 8: Xiao KJ, Wang Y, Ye KY, Huang PQ. Versatile one-pot reductive alkylation of lactams/amides via amide activation: application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine. Chemistry. 2010 Nov 15;16(43):12792-6. doi: 10.1002/chem.201002054. PubMed PMID: 20938943. 9: Rizzi D, Basile C, Di Maggio A, Sebastio A, Introna F Jr, Rizzi R, Bruno S, Scatizzi A, De Marco S. Rhabdomyolysis and acute tubular necrosis in coniine (hemlock) poisoning. Lancet. 1989 Dec 16;2(8677):1461-2. PubMed PMID: 2574394. 10: LAGRUTTA V, DESMEDT JE. [CONTRASTS BETWEEN THE CENTRAL ACTIONS OF CONIINE AND STRYCHNINE]. Arch Int Pharmacodyn Ther. 1964 Sep 1;151:289-96. French. PubMed PMID: 14205424. 11: Frank AA, Reed WM. Comparative toxicity of coniine, an alkaloid of Conium maculatum (poison hemlock), in chickens, quails, and turkeys. Avian Dis. 1990 Apr-Jun;34(2):433-7. PubMed PMID: 2369382. 12: Beng TK, Gawley RE. Highly enantioselective catalytic dynamic resolution of N-Boc-2-lithiopiperidine: synthesis of (R)-(+)-N-Boc-pipecolic acid, (S)-(-)-coniine, (S)-(+)-pelletierine, (+)-beta-conhydrine, and (S)-(-)-ropivacaine and formal synthesis of (-)-lasubine II and (+)-cermizine C. J Am Chem Soc. 2010 Sep 8;132(35):12216-7. doi: 10.1021/ja105772z. PubMed PMID: 20806976; PubMed Central PMCID: PMC2945905. 13: Hotti H, Seppänen-Laakso T, Arvas M, Teeri TH, Rischer H. Polyketide synthases from poison hemlock (Conium maculatum L.). FEBS J. 2015 Nov;282(21):4141-56. doi: 10.1111/febs.13410. Epub 2015 Sep 11. PubMed PMID: 26260860. 14: Burke AJ, Davies SG, Garner AC, McCarthy TD, Roberts PM, Smith AD, Rodriguez-Solla H, Vickers RJ. Asymmetric synthesis and applications of beta-amino Weinreb amides: asymmetric synthesis of (S)-coniine. Org Biomol Chem. 2004 May 7;2(9):1387-94. Epub 2004 Apr 5. PubMed PMID: 15105931. 15: Green BT, Lee ST, Panter KE, Welch KD, Cook D, Pfister JA, Kem WR. Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicol Teratol. 2010 May-Jun;32(3):383-90. doi: 10.1016/j.ntt.2010.01.011. Epub 2010 Jan 29. PubMed PMID: 20116429. 16: de BOER J. The death of Socrates. A historical and experimental study on the actions of coniine and conium maculatum. Arch Int Pharmacodyn Ther. 1950 Sep 1;83(4):473-90. PubMed PMID: 14777599. 17: NALEGATSKAIA AV. [Resistance of white mice to coniine in various periods of postnatal development]. Farmakol Toksikol. 1958 Sep-Oct;21(5):85-6. Russian. PubMed PMID: 13609694. 18: Wilkinson TJ, Stehle NW, Beak P. Enantioselective syntheses of 2-alkyl- and 2,6-dialkylpiperidine alkaloids: preparations of the hydrochlorides of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine. Org Lett. 2000 Jan 27;2(2):155-8. PubMed PMID: 10814270. 19: Sampson SR. Mechanism of coniine-blockade of postsynaptic inhibition in the spinal cord of the cat. Int J Neuropharmacol. 1966 Mar;5(2):171-82. PubMed PMID: 5959956. 20: SAMPSON SR, ESPLIN DW, ZABLOCKA B. NEUROPHARMACOLOGICAL ANALYSIS OF THE EFFECTS OF CONIINE. Proc West Pharmacol Soc. 1963;6:4-6. PubMed PMID: 14062835.

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